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    Inverting the diastereoselectivity of the mukaiyama-michael addition with graphite-based catalysts

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    Type
    Article
    Authors
    Acocella, Maria Rosaria
    Mauro, Marco
    Falivene, Laura cc
    Cavallo, Luigi cc
    Guerra, Gaetano
    KAUST Department
    Chemical Science Program
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2014-01-08
    Online Publication Date
    2014-01-08
    Print Publication Date
    2014-02-07
    Permanent link to this record
    http://hdl.handle.net/10754/563388
    
    Metadata
    Show full item record
    Abstract
    Here, we show that graphite-based catalysts, mainly graphite oxide (GO) and exfoliated GO, are effective recyclable catalysts for a relevant stereoselective Mukaiyama-Michael addition, outperforming currently available catalysts. Moreover, the graphite-based catalysts described here invert the diastereoselectivity relative to that observed with known catalysts, with the unprecedented large prevalence of the anti diastereoisomer. This inverted diastereoselectivity is increased when the catalyst concentration is reduced and after catalyst recycling. Density functional theory calculations suggest that the selectivity is determined by two types of supramolecular interactions operating between the catalyst and the substrates at the diastereoselectivity- determining transition state, specifically, the π-stacking of b-nitrostyrene with graphite and the van der Waals interaction between the SiMe3 group of the silyl ether and the graphite. © 2013 American Chemical Society.
    Citation
    Acocella, M. R., Mauro, M., Falivene, L., Cavallo, L., & Guerra, G. (2014). Inverting the Diastereoselectivity of the Mukaiyama–Michael Addition with Graphite-Based Catalysts. ACS Catalysis, 4(2), 492–496. doi:10.1021/cs401053t
    Sponsors
    We thank Prof. Arrigo Scettri, Dr. Marialuigia Raimondo, and Prof. Liberata Guadagno for useful discussions. The Ministero dell' Istruzione dell' Universita e della Ricerca is gratefully acknowledged for financial support (PRIN).
    Publisher
    American Chemical Society (ACS)
    Journal
    ACS Catalysis
    DOI
    10.1021/cs401053t
    ae974a485f413a2113503eed53cd6c53
    10.1021/cs401053t
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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